Alestramustine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Alestramustine
Alestramustine.svg
Clinical data
SynonymsEstradiol 3-(bis(2-chloroethyl)carbamate) 17β-(L-alaninate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(2β-aminopropanoate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-((2S)-2-aminopropanoate)
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H36Cl2N2O4
Molar mass511.481 g/mol g·mol−1
3D model (JSmol)

Alestramustine (INN), also known as estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed.[1][2] It is the L-alanine ester of estramustine, which is a combination of the nitrogen mustard normustine coupled via a carbamate to the estrogen estradiol.[1][3] Alestramustine acts as a prodrug to estramustine, and also forms estradiol as a byproduct.[1][3] The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division.[1][3] Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.[1]

See also[edit]

References[edit]

  1. ^ a b c d e NCI Thesaurus. "Alestramustine". Retrieved 24 June 2016.
  2. ^ G. W. A. Milne (1 July 2000). Ashgate Handbook of Antineoplastic Agents. Wiley. p. 5. ISBN 978-0-566-08382-2.
  3. ^ a b c KD Tripathi (30 September 2013). Essentials of Medical Pharmacology. JP Medical Ltd. pp. 866–. ISBN 978-93-5025-937-5.